Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Ethyl 1-[6-(2-{[4-(2-phenylethyl)benzyl]oxy}phenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate | HCID 67159203 | — |
| Product | Trifluoroacetic acid | HCID 6422 | — |
| Product | 1-[6-(2-{[4-(2-Phenylethyl)benzyl]oxy}phenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid | HCID 25233125 | — |
Reaction Steps
To a solution of the title compound from Example 1 Step C (27.0 mg, 0.048 mmol) in 1,4-dioxane (2 mL) was added lithium hydroxide (1.0 mL, 2.0 M aqueous, 2.0 mmol), and the resulting mixture was stirred at 60° C. After 15 min, the reaction mixture was rendered acidic by addition of aqueous hydrochloric acid, then was diluted with 1,4-dioxane and passed through a 0.45 micron syringe filter. Purification by reverse phase HPLC (30 to 100% acetonitrile in water, each with 0.1% v/v TFA) provided the title compound: LCMS m/z 544.4 [M+H]+; 1H NMR (500 MHz, d6-DMSO) δ 8.25 (s, 1H), 8.14-8.07 (m, 2H), 7.74 (d, J=7.5 Hz, 1H), 7.69 (d, J=7.5 Hz, 1H), 7.42 (t, J=7.5 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 7.27-7.14 (m, 8H), 7.09 (t, J=8.0 Hz, 1H), 5.19 (s, 2H), 2.86 (app s, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08455638B2 |
|---|
| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-8d15f1a163d84cf185640e091a810629 |
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| Source note | uspto-grants-2013_06 |
|---|
